Associate Retention Specialist

life insurance, parental leave, paid time off, paid holidays, tuition reimbursement, 401(k)

Jul 27, 2026

The Associate Retention Specialist is responsible for driving trial customer engagement, automated outreach strategy and deployment and retention initiatives across our government customer base. This role serves as the operational owner for customer-facing engagement programs that help accelerate product adoption, improve trial conversion, support retention efforts, and increase customer awareness of our government product suite.

The role partners closely with Sales, Customer Success, Marketing, Revenue Management, and GTM Strategy teams to execute scalable engagement motions that drive revenue growth and customer outcomes.

In this opportunity as an Associate Retention Specialist, you will:

• Manage the Government Checkpoint customer portfolio, focusing on retention, and renewal support.
• Coordinate outreach strategies that increase trial participation, product usage, and sales conversions.
• Partner with sales teams to ensure trial customers receive targeted resources, training, and follow-up engagement.
• Serve as the Government business lead for HVS campaigns and Salesforce Sales Engagement programs.
• Build, manage, and deploy scalable outreach cadences supporting strategic campaigns and demand generation efforts.
• Train and support sales representatives on HVS best practices, campaign execution, and engagement analytics.
• Monitor campaign performance and provide recommendations to improve meeting generation, pipeline creation, and revenue outcomes.
• Create and maintain customer-facing content, digital sales rooms, trial materials, onboarding resources, and product education assets.
• Support sales teams with messaging, engagement tools, campaign templates, and customer leave-behinds.
• Deliver training sessions and best-practice guidance for customer engagement platforms and outreach programs.

You're a fit for the role of Associate Retention Specialist if you have:

• Bachelor's degree or equivalent experience.
• 3+ years in customer success, sales operations, account management, or retention.
• Experience managing customer-engagement, trial-conversion, or retention campaigns.
• Proficiency with Salesforce and sales-engagement tools (e.g., HVS, Outreach, Salesloft).
• Strong understanding of customer lifecycle and sales metrics, including adoption, conversion, retention, and pipeline.
• Excellent communication, content development, training, and cross-functional collaboration skills.
• Strong organizational, project-management, and analytical abilities.
• Government/public-sector or SaaS experience preferred.

• Flexibility & Work-Life Balance: Flex My Way is a set of supportive workplace policies designed to help manage personal and professional responsibilities, whether caring for family, giving back to the community, or finding time to refresh and reset. This builds upon our flexible work arrangements, including work from anywhere for up to 8 weeks per year, empowering employees to achieve a better work-life balance.
• Career Development and Growth: By fostering a culture of continuous learning and skill development, we prepare our talent to tackle tomorrow's challenges and deliver real-world solutions. Our Grow My Way programming and skills-first approach ensures you have the tools and knowledge to grow, lead, and thrive in an AI-enabled future.
• Industry Competitive Benefits: We offer comprehensive benefit plans to include flexible vacation, two company-wide Mental Health Days off, access to the Headspace app, retirement savings, tuition reimbursement, employee incentive programs, and resources for mental, physical, and financial wellbeing.
• Culture: Globally recognized, award-winning reputation for inclusion and belonging, flexibility, work-life balance, and more. We live by our values:
  Obsess over our Customers, Compete to Win, Challenge (Y) our Thinking, Act Fast / Learn Fast, and Stronger Together.
• Social Impact: Make an impact in your community with our Social Impact Institute. We offer employees two paid volunteer days off annually and opportunities to get…